Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca)

Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Smedley, Scott R. [verfasserIn] Risteen, Riley G. Tonyai, Kathareeya K. Pitino, Julia C. Hu, Yunming Ahmed, Zenab B. Christofel, Brian T. Gaber, Maha Howells, Nicole R. Mosey, Connor F. Rahim, Faizan U. Deyrup, Stephen T.

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2017

Schlagwörter:	Lampyridae Lucibufagin Bufadienolide Chemical defense Reflex bleeding

Anmerkung:	© Springer International Publishing AG 2017

Übergeordnetes Werk:	Enthalten in: Chemoecology - Cham : Springer International Publishing AG, 1990, 27(2017), 4 vom: 20. Juli, Seite 141-153
Übergeordnetes Werk:	volume:27 ; year:2017 ; number:4 ; day:20 ; month:07 ; pages:141-153

Links:	Volltext

DOI / URN:	10.1007/s00049-017-0240-6

Katalog-ID:	SPR000428183

Internformat


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100	1		\|a Smedley, Scott R. \|e verfasserin \|4 aut
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520			\|a Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically.
650		4	\|a Lampyridae \|7 (dpeaa)DE-He213
650		4	\|a Lucibufagin \|7 (dpeaa)DE-He213
650		4	\|a Bufadienolide \|7 (dpeaa)DE-He213
650		4	\|a Chemical defense \|7 (dpeaa)DE-He213
650		4	\|a Reflex bleeding \|7 (dpeaa)DE-He213
700	1		\|a Risteen, Riley G. \|4 aut
700	1		\|a Tonyai, Kathareeya K. \|4 aut
700	1		\|a Pitino, Julia C. \|4 aut
700	1		\|a Hu, Yunming \|4 aut
700	1		\|a Ahmed, Zenab B. \|4 aut
700	1		\|a Christofel, Brian T. \|4 aut
700	1		\|a Gaber, Maha \|4 aut
700	1		\|a Howells, Nicole R. \|4 aut
700	1		\|a Mosey, Connor F. \|4 aut
700	1		\|a Rahim, Faizan U. \|4 aut
700	1		\|a Deyrup, Stephen T. \|4 aut
773	0	8	\|i Enthalten in \|t Chemoecology \|d Cham : Springer International Publishing AG, 1990 \|g 27(2017), 4 vom: 20. Juli, Seite 141-153 \|w (DE-627)253390591 \|w (DE-600)1458504-2 \|x 1423-0445 \|7 nnns
773	1	8	\|g volume:27 \|g year:2017 \|g number:4 \|g day:20 \|g month:07 \|g pages:141-153
856	4	0	\|u https://dx.doi.org/10.1007/s00049-017-0240-6 \|z lizenzpflichtig \|3 Volltext
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912			\|a GBV_ILN_74
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912			\|a GBV_ILN_101
912			\|a GBV_ILN_105
912			\|a GBV_ILN_110
912			\|a GBV_ILN_120
912			\|a GBV_ILN_138
912			\|a GBV_ILN_150
912			\|a GBV_ILN_151
912			\|a GBV_ILN_152
912			\|a GBV_ILN_161
912			\|a GBV_ILN_170
912			\|a GBV_ILN_171
912			\|a GBV_ILN_187
912			\|a GBV_ILN_213
912			\|a GBV_ILN_224
912			\|a GBV_ILN_230
912			\|a GBV_ILN_250
912			\|a GBV_ILN_267
912			\|a GBV_ILN_281
912			\|a GBV_ILN_285
912			\|a GBV_ILN_293
912			\|a GBV_ILN_370
912			\|a GBV_ILN_602
912			\|a GBV_ILN_636
912			\|a GBV_ILN_702
912			\|a GBV_ILN_2001
912			\|a GBV_ILN_2003
912			\|a GBV_ILN_2004
912			\|a GBV_ILN_2005
912			\|a GBV_ILN_2006
912			\|a GBV_ILN_2007
912			\|a GBV_ILN_2008
912			\|a GBV_ILN_2009
912			\|a GBV_ILN_2010
912			\|a GBV_ILN_2011
912			\|a GBV_ILN_2014
912			\|a GBV_ILN_2015
912			\|a GBV_ILN_2020
912			\|a GBV_ILN_2021
912			\|a GBV_ILN_2025
912			\|a GBV_ILN_2026
912			\|a GBV_ILN_2027
912			\|a GBV_ILN_2031
912			\|a GBV_ILN_2034
912			\|a GBV_ILN_2037
912			\|a GBV_ILN_2038
912			\|a GBV_ILN_2039
912			\|a GBV_ILN_2044
912			\|a GBV_ILN_2048
912			\|a GBV_ILN_2049
912			\|a GBV_ILN_2050
912			\|a GBV_ILN_2055
912			\|a GBV_ILN_2057
912			\|a GBV_ILN_2059
912			\|a GBV_ILN_2061
912			\|a GBV_ILN_2064
912			\|a GBV_ILN_2065
912			\|a GBV_ILN_2068
912			\|a GBV_ILN_2070
912			\|a GBV_ILN_2086
912			\|a GBV_ILN_2088
912			\|a GBV_ILN_2093
912			\|a GBV_ILN_2106
912			\|a GBV_ILN_2107
912			\|a GBV_ILN_2108
912			\|a GBV_ILN_2110
912			\|a GBV_ILN_2111
912			\|a GBV_ILN_2112
912			\|a GBV_ILN_2113
912			\|a GBV_ILN_2116
912			\|a GBV_ILN_2118
912			\|a GBV_ILN_2119
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912			\|a GBV_ILN_2153
912			\|a GBV_ILN_2188
912			\|a GBV_ILN_2190
912			\|a GBV_ILN_2232
912			\|a GBV_ILN_2336
912			\|a GBV_ILN_2446
912			\|a GBV_ILN_2470
912			\|a GBV_ILN_2472
912			\|a GBV_ILN_2507
912			\|a GBV_ILN_2522
912			\|a GBV_ILN_2548
912			\|a GBV_ILN_4012
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4046
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4126
912			\|a GBV_ILN_4242
912			\|a GBV_ILN_4246
912			\|a GBV_ILN_4249
912			\|a GBV_ILN_4251
912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4306
912			\|a GBV_ILN_4307
912			\|a GBV_ILN_4313
912			\|a GBV_ILN_4322
912			\|a GBV_ILN_4323
912			\|a GBV_ILN_4324
912			\|a GBV_ILN_4325
912			\|a GBV_ILN_4326
912			\|a GBV_ILN_4333
912			\|a GBV_ILN_4334
912			\|a GBV_ILN_4335
912			\|a GBV_ILN_4336
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951			\|a AR
952			\|d 27 \|j 2017 \|e 4 \|b 20 \|c 07 \|h 141-153

Indexfelder

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matchkey_str	article:14230445:2017----::uainldsuiuaisrmnclgclybratie
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publishDate	2017
allfields	10.1007/s00049-017-0240-6 doi (DE-627)SPR000428183 (SPR)s00049-017-0240-6-e DE-627 ger DE-627 rakwb eng Smedley, Scott R. verfasserin aut Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca) 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer International Publishing AG 2017 Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically. Lampyridae (dpeaa)DE-He213 Lucibufagin (dpeaa)DE-He213 Bufadienolide (dpeaa)DE-He213 Chemical defense (dpeaa)DE-He213 Reflex bleeding (dpeaa)DE-He213 Risteen, Riley G. aut Tonyai, Kathareeya K. aut Pitino, Julia C. aut Hu, Yunming aut Ahmed, Zenab B. aut Christofel, Brian T. aut Gaber, Maha aut Howells, Nicole R. aut Mosey, Connor F. aut Rahim, Faizan U. aut Deyrup, Stephen T. aut Enthalten in Chemoecology Cham : Springer International Publishing AG, 1990 27(2017), 4 vom: 20. Juli, Seite 141-153 (DE-627)253390591 (DE-600)1458504-2 1423-0445 nnns volume:27 year:2017 number:4 day:20 month:07 pages:141-153 https://dx.doi.org/10.1007/s00049-017-0240-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2017 4 20 07 141-153
spelling	10.1007/s00049-017-0240-6 doi (DE-627)SPR000428183 (SPR)s00049-017-0240-6-e DE-627 ger DE-627 rakwb eng Smedley, Scott R. verfasserin aut Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca) 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer International Publishing AG 2017 Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically. Lampyridae (dpeaa)DE-He213 Lucibufagin (dpeaa)DE-He213 Bufadienolide (dpeaa)DE-He213 Chemical defense (dpeaa)DE-He213 Reflex bleeding (dpeaa)DE-He213 Risteen, Riley G. aut Tonyai, Kathareeya K. aut Pitino, Julia C. aut Hu, Yunming aut Ahmed, Zenab B. aut Christofel, Brian T. aut Gaber, Maha aut Howells, Nicole R. aut Mosey, Connor F. aut Rahim, Faizan U. aut Deyrup, Stephen T. aut Enthalten in Chemoecology Cham : Springer International Publishing AG, 1990 27(2017), 4 vom: 20. Juli, Seite 141-153 (DE-627)253390591 (DE-600)1458504-2 1423-0445 nnns volume:27 year:2017 number:4 day:20 month:07 pages:141-153 https://dx.doi.org/10.1007/s00049-017-0240-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2017 4 20 07 141-153
allfields_unstemmed	10.1007/s00049-017-0240-6 doi (DE-627)SPR000428183 (SPR)s00049-017-0240-6-e DE-627 ger DE-627 rakwb eng Smedley, Scott R. verfasserin aut Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca) 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer International Publishing AG 2017 Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically. Lampyridae (dpeaa)DE-He213 Lucibufagin (dpeaa)DE-He213 Bufadienolide (dpeaa)DE-He213 Chemical defense (dpeaa)DE-He213 Reflex bleeding (dpeaa)DE-He213 Risteen, Riley G. aut Tonyai, Kathareeya K. aut Pitino, Julia C. aut Hu, Yunming aut Ahmed, Zenab B. aut Christofel, Brian T. aut Gaber, Maha aut Howells, Nicole R. aut Mosey, Connor F. aut Rahim, Faizan U. aut Deyrup, Stephen T. aut Enthalten in Chemoecology Cham : Springer International Publishing AG, 1990 27(2017), 4 vom: 20. Juli, Seite 141-153 (DE-627)253390591 (DE-600)1458504-2 1423-0445 nnns volume:27 year:2017 number:4 day:20 month:07 pages:141-153 https://dx.doi.org/10.1007/s00049-017-0240-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2017 4 20 07 141-153
allfieldsGer	10.1007/s00049-017-0240-6 doi (DE-627)SPR000428183 (SPR)s00049-017-0240-6-e DE-627 ger DE-627 rakwb eng Smedley, Scott R. verfasserin aut Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca) 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer International Publishing AG 2017 Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically. Lampyridae (dpeaa)DE-He213 Lucibufagin (dpeaa)DE-He213 Bufadienolide (dpeaa)DE-He213 Chemical defense (dpeaa)DE-He213 Reflex bleeding (dpeaa)DE-He213 Risteen, Riley G. aut Tonyai, Kathareeya K. aut Pitino, Julia C. aut Hu, Yunming aut Ahmed, Zenab B. aut Christofel, Brian T. aut Gaber, Maha aut Howells, Nicole R. aut Mosey, Connor F. aut Rahim, Faizan U. aut Deyrup, Stephen T. aut Enthalten in Chemoecology Cham : Springer International Publishing AG, 1990 27(2017), 4 vom: 20. Juli, Seite 141-153 (DE-627)253390591 (DE-600)1458504-2 1423-0445 nnns volume:27 year:2017 number:4 day:20 month:07 pages:141-153 https://dx.doi.org/10.1007/s00049-017-0240-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2017 4 20 07 141-153
allfieldsSound	10.1007/s00049-017-0240-6 doi (DE-627)SPR000428183 (SPR)s00049-017-0240-6-e DE-627 ger DE-627 rakwb eng Smedley, Scott R. verfasserin aut Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca) 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer International Publishing AG 2017 Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically. Lampyridae (dpeaa)DE-He213 Lucibufagin (dpeaa)DE-He213 Bufadienolide (dpeaa)DE-He213 Chemical defense (dpeaa)DE-He213 Reflex bleeding (dpeaa)DE-He213 Risteen, Riley G. aut Tonyai, Kathareeya K. aut Pitino, Julia C. aut Hu, Yunming aut Ahmed, Zenab B. aut Christofel, Brian T. aut Gaber, Maha aut Howells, Nicole R. aut Mosey, Connor F. aut Rahim, Faizan U. aut Deyrup, Stephen T. aut Enthalten in Chemoecology Cham : Springer International Publishing AG, 1990 27(2017), 4 vom: 20. Juli, Seite 141-153 (DE-627)253390591 (DE-600)1458504-2 1423-0445 nnns volume:27 year:2017 number:4 day:20 month:07 pages:141-153 https://dx.doi.org/10.1007/s00049-017-0240-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2017 4 20 07 141-153
language	English
source	Enthalten in Chemoecology 27(2017), 4 vom: 20. Juli, Seite 141-153 volume:27 year:2017 number:4 day:20 month:07 pages:141-153
sourceStr	Enthalten in Chemoecology 27(2017), 4 vom: 20. Juli, Seite 141-153 volume:27 year:2017 number:4 day:20 month:07 pages:141-153
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	Lampyridae Lucibufagin Bufadienolide Chemical defense Reflex bleeding
isfreeaccess_bool	false
container_title	Chemoecology
authorswithroles_txt_mv	Smedley, Scott R. @@aut@@ Risteen, Riley G. @@aut@@ Tonyai, Kathareeya K. @@aut@@ Pitino, Julia C. @@aut@@ Hu, Yunming @@aut@@ Ahmed, Zenab B. @@aut@@ Christofel, Brian T. @@aut@@ Gaber, Maha @@aut@@ Howells, Nicole R. @@aut@@ Mosey, Connor F. @@aut@@ Rahim, Faizan U. @@aut@@ Deyrup, Stephen T. @@aut@@
publishDateDaySort_date	2017-07-20T00:00:00Z
hierarchy_top_id	253390591
id	SPR000428183
language_de	englisch
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author	Smedley, Scott R.
spellingShingle	Smedley, Scott R. misc Lampyridae misc Lucibufagin misc Bufadienolide misc Chemical defense misc Reflex bleeding Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca)
authorStr	Smedley, Scott R.
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topic_title	Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca) Lampyridae (dpeaa)DE-He213 Lucibufagin (dpeaa)DE-He213 Bufadienolide (dpeaa)DE-He213 Chemical defense (dpeaa)DE-He213 Reflex bleeding (dpeaa)DE-He213
topic	misc Lampyridae misc Lucibufagin misc Bufadienolide misc Chemical defense misc Reflex bleeding
topic_unstemmed	misc Lampyridae misc Lucibufagin misc Bufadienolide misc Chemical defense misc Reflex bleeding
topic_browse	misc Lampyridae misc Lucibufagin misc Bufadienolide misc Chemical defense misc Reflex bleeding
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title	Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca)
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title_full	Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca)
author_sort	Smedley, Scott R.
journal	Chemoecology
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author_browse	Smedley, Scott R. Risteen, Riley G. Tonyai, Kathareeya K. Pitino, Julia C. Hu, Yunming Ahmed, Zenab B. Christofel, Brian T. Gaber, Maha Howells, Nicole R. Mosey, Connor F. Rahim, Faizan U. Deyrup, Stephen T.
container_volume	27
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author-letter	Smedley, Scott R.
doi_str_mv	10.1007/s00049-017-0240-6
title_sort	bufadienolides (lucibufagins) from an ecologically aberrant firefly (ellychnia corrusca)
title_auth	Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca)
abstract	Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically. © Springer International Publishing AG 2017
abstractGer	Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically. © Springer International Publishing AG 2017
abstract_unstemmed	Abstract The winter firefly (Ellychnia corrusca) is common throughout the eastern United States and Canada. It is notable among fireflies (Coleoptera: Lampyridae) for its adult activity during the winter and early spring months, and for its lack of a light-producing organ. Multiple lines of evidence suggest that E. corrusca is chemically protected, specifically its unusual phenology which results in prolonged exposure to predators, its aposematic coloration, its reflex bleeding upon disturbance, and its relatedness to toxic firefly genera. Chemical investigation of this species revealed the presence of large quantities (>500 μg/beetle) of steroidal pyrones known as lucibufagins. The structures of these lucibufagins were determined using 1D and 2D NMR spectroscopy along with UHPLC-HRMS. Four of these compounds were previously detected in fireflies of the genus Photinus, while the remaining four, which contain a highly modified D-ring of the steroid core, are previously unknown. Analysis of reflex bleeding showed that the hemolymph contained the lucibufagins and that it was primarily released via a band of cuticular pores along the costal margin of the elytra. In addition, our analysis of the eggs, larva, and pupa established that all immature stages possess lucibufagins, thus representing the first instance of a firefly species for which all life stages have been investigated chemically. © Springer International Publishing AG 2017
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container_issue	4
title_short	Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca)
url	https://dx.doi.org/10.1007/s00049-017-0240-6
remote_bool	true
author2	Risteen, Riley G. Tonyai, Kathareeya K. Pitino, Julia C. Hu, Yunming Ahmed, Zenab B. Christofel, Brian T. Gaber, Maha Howells, Nicole R. Mosey, Connor F. Rahim, Faizan U. Deyrup, Stephen T.
author2Str	Risteen, Riley G. Tonyai, Kathareeya K. Pitino, Julia C. Hu, Yunming Ahmed, Zenab B. Christofel, Brian T. Gaber, Maha Howells, Nicole R. Mosey, Connor F. Rahim, Faizan U. Deyrup, Stephen T.
ppnlink	253390591
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doi_str	10.1007/s00049-017-0240-6
up_date	2024-07-03T16:01:26.551Z
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Bufadienolides (lucibufagins) from an ecologically aberrant firefly (Ellychnia corrusca)

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